JPS6232742B2 - - Google Patents

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Publication number
JPS6232742B2
JPS6232742B2 JP186879A JP186879A JPS6232742B2 JP S6232742 B2 JPS6232742 B2 JP S6232742B2 JP 186879 A JP186879 A JP 186879A JP 186879 A JP186879 A JP 186879A JP S6232742 B2 JPS6232742 B2 JP S6232742B2
Authority
JP
Japan
Prior art keywords
group
hydrogen atom
herbicide
compound according
formula
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
JP186879A
Other languages
Japanese (ja)
Other versions
JPS5594353A (en
Inventor
Tetsuo Takematsu
Kyoaki Niuchi
Yoshinori Tanaka
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mitsui Toatsu Chemicals Inc
Original Assignee
Mitsui Toatsu Chemicals Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Mitsui Toatsu Chemicals Inc filed Critical Mitsui Toatsu Chemicals Inc
Priority to JP186879A priority Critical patent/JPS5594353A/en
Publication of JPS5594353A publication Critical patent/JPS5594353A/en
Publication of JPS6232742B2 publication Critical patent/JPS6232742B2/ja
Granted legal-status Critical Current

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  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Description

【発明の詳細な説明】[Detailed description of the invention]

本発明は新規なフエノキシフエニルカーバメー
ト誘導体、その製造方法およびその用途に係わる
ものである。詳しくは一般式 (式中、R1およびR2はそれぞれ水素原子、低級ア
ルキル基、フエニル基またはハロゲン置換フエニ
ル基を示す。)で表わされる化合物と、その製造
方法およびこれらの少くとも一種を有効成分とし
て含有することを特徴とする除草剤に関するもの
である。 本発明は、特に除草剤として有用な新規なフエ
ノキシフエニルカーバメート誘導体を提供しよう
とするものである。 また、本発明は新期なフエノキシフエニルカー
バメート誘導体を有利に製造するための方法を提
供しようとするものである。 さらに、本発明は、特にイネ科属間選択性が優
れた除草剤を提供しようとするものである。 本発明者らは、これまでジフエニルエーテル系
除草剤がイネに薬害が少ないことに着眼し研究を
進めてきたが、近年遂次領域を増大しつつある還
元性土壌に施用しても、効力を失わない化合物、
すなわちニトロ基を含有しない新規ジフエニルエ
ーテル系化合物を探索した結果、本発明化合物が
除草剤として多くの、すぐれた特徴を有すること
を発見して本発明を完成するに至つた。 本発明のカルバミン酸フエノキシフエニル誘導
体は下記の反応式(1)〜(3)に従つて、工業的に有利
に製造されうる。 (式中、R1およびR2は先に特許請求の範囲に記載
したものと同意義であり、Mは水素原子、カリウ
ム原子またはナトリウム原子であり、Xは塩素原
子または臭素原子を示す) すなわち、前記反応式(1)においては、フエノキ
シフエノール〔〕を適当な溶媒に溶かし、これ
に同じ溶媒にとかしたイソシアネート、またはイ
ソシアネートと触媒を加えて−20〜50℃で1〜5
時間反応させたのち、脱溶媒し、少量の溶媒を加
えて再結晶化するか、減圧蒸留またはカラムクロ
マトグラフイーを用いて分離することによつて、
本発明の化合物〔〕を好収率で得ることができ
る。反応溶媒としてはベンゼン、トルエン、ケト
ン類、エーテル類またはジオキサンなどがある。
触媒としてはトリエチルアミンやピリジンなどの
有機塩基がよく、再結晶溶媒はベンゼンやトルエ
ンを使用できる。反応温度は好ましくは0℃〜室
温である。 反応式(2)ではフエノキシフエノールのナトリウ
ム塩またはカリウム塩〔′〕をイソプロパノー
ル、アセトン、メチルエチルケトン、ベンゼン、
トルエンまたはクロロホルムなどの溶媒中に懸濁
し、N・N−ジ置換カルバモイルハライド〔〕
を加えて−20〜80℃で2〜6時間反応させる。こ
の場合、フエノキシフエノールとカセイカリ、炭
酸カリ、カセイソーダ、ジメチルアニリン、トリ
エチルアミンまたはピリジンなどの脱酸剤の共存
下で、N・N−ジ置換カルバモイルハライドを同
様に反応させてもよい。以上の反応により、本発
明の化合物〔〕を得ることができる。 反応式(3)では、フエノキシフエノールをアセト
ン、メチルエチルケトン、ベンゼン、トルエン、
またはクロロホルムなどにとかし、これとカルボ
ニルジハライドとを室温で反応させて、ハロ蟻酸
フエノキシフエニルエステル〔〕を得る。
〔〕は空気中の水分などで分解し易いため、通
常これを単離せず、上記反応液中の生成ハロゲン
化水素および過剰の溶解カルボニルジハライドを
減圧除去したのち、倍モル量のアミンと反応させ
る。生成したアミンのハロゲン化水素塩塩をろ別
し、溶媒を留去したのち、反応式(1)と同様な精製
方法によつて、本発明の化合物〔〕を得ること
ができる。 次に実施例をあげて、本発明の製造方法につい
て詳しく説明する。 実施例 1 3−(2−クロル−4−トリフルオルメチルフ
エノキシ)フエニルN−メチルカーバメートの
合成 3−(2−クロル−4−トリフルオルメチルフ
エノキシ)フエノール5gを50mlの無水ベンゼン
に溶解し、この溶液に3gのメチルイソシアナー
トと0.1mlのトリエチルアミンを加え、室温で3
時間撹拌した。反応終了後、溶媒を減圧下に除去
し、油状物を得、これを、少量のベンゼンで再結
晶し、目的物4.6gを得た。 実施例 2 3−(2−クロル−4−トリフルオルメチルフ
エノキシ)フエニルN・N−ジメチルカーバメ
ートの合成 3−(2−クロル−4−トリフルオルメチルフ
エノキシ)フエノールのカリウム塩7gを50mlの
メチルエチルケトンに懸濁させ、これにジメチル
カルバミン酸クロライド4gを加え、室温で1時
間撹拌した。反応終了後、内容物を300mlの水中
に投入し、酢酸エチルにて抽出した。抽出相を水
洗し、芒硝で乾燥後、酢酸エチルを留去し、残留
物をカラムクロマトグラフイー(シリカゲル、展
開溶媒;ベンゼン:酢酸エチル=50:1)を用い
て精製した。n181.5270の目的物5.8gを得
た。 実施例 3 3−(2−クロル−4−トリフルオルメチルフ
エノキシ)フエニルN・N−ジエチルカーバメ
ートの合成 3−(2−クロル−4−トリフルオルメチルフ
エノキシ)フエノール7gをメチルエチルケトン
に溶解し、これに5gの炭酸カリウム、5gのジ
エチルカルバミン酸クロライドを加え、加熱還流
下5時間撹拌した。反応終了後、固型物を吸引ロ
別したのち、メチルエチルケトンを留去し、残留
物をカラムクロマトグラフイー(シリカゲル、展
開溶媒;ベンゼン:酢酸エチル=50:1)を用い
て精製した。n181.5208の目的物4.5gを得
た。 実施例 4 20℃でトルエン100mlにホスゲン11gを吸収さ
せ、3−(2−クロル−4−トリフルオルメチル
フエノキシ)フエノール28.9gを加え、液温を20
〜25℃に保ちながら45%水酸化ナトリウム水溶液
12.5gを滴下したのち、30分間かきまぜて反応を
完結させた。ついで水80mlで2回、2%水酸化ナ
トリウム100mlで1回洗浄した。かくして得た3
−(2−クロル−4−トリフルオルメチルフエノ
キシ)フエニルクロルホーメートのトルエン溶液
を15〜20℃に保ち、強くかきまぜながら、50%ジ
メチルアミン12.6gを加えた。さらに20%水酸化
ナトリウム水溶液14mlを滴下し、同温度で1時間
反応させた後、反応液を冷水200mlで3回繰返し
て洗浄した。ついでトルエン層を無水硫酸ナトリ
ウムで脱水し、減圧下60℃以下でトルエンを留去
した。残部をカラムクロマトグラフイー(シリカ
ゲル、展開溶媒;ベンゼン:n−ヘキサン=1:
1)で精製し、n181.5270の目的物31.2gを
得た。 前記の本発明製造法によつて得られた代表的な
化合物とその物性、元素分析値を下記の第1表に
記載する。
The present invention relates to a novel phenoxyphenyl carbamate derivative, a method for producing the same, and uses thereof. For details, see the general formula (In the formula, R 1 and R 2 each represent a hydrogen atom, a lower alkyl group, a phenyl group, or a halogen-substituted phenyl group.), a method for producing the same, and at least one of these as an active ingredient. The present invention relates to a herbicide characterized by the following. The present invention seeks to provide novel phenoxyphenyl carbamate derivatives that are particularly useful as herbicides. The present invention also provides a method for advantageously producing a new phenoxyphenyl carbamate derivative. Furthermore, the present invention aims to provide a herbicide with particularly excellent selectivity among Poaceae genera. The present inventors have so far conducted research focusing on the fact that diphenyl ether herbicides have little phytotoxicity on rice. Compounds that do not lose
That is, as a result of searching for a new diphenyl ether compound that does not contain a nitro group, it was discovered that the compound of the present invention has many excellent characteristics as a herbicide, leading to the completion of the present invention. The phenoxyphenyl carbamate derivatives of the present invention can be advantageously produced industrially according to the following reaction formulas (1) to (3). (In the formula, R 1 and R 2 have the same meanings as described in the claims above, M is a hydrogen atom, a potassium atom, or a sodium atom, and X represents a chlorine atom or a bromine atom) In the above reaction formula (1), phenoxyphenol [ ] is dissolved in a suitable solvent, and an isocyanate dissolved in the same solvent, or an isocyanate and a catalyst are added thereto, and the mixture is heated at -20 to 50°C for 1 to 5 hours.
After reacting for a period of time, the solvent is removed and recrystallized by adding a small amount of solvent, or by separation using vacuum distillation or column chromatography.
The compound of the present invention [] can be obtained in good yield. Examples of the reaction solvent include benzene, toluene, ketones, ethers, and dioxane.
As a catalyst, an organic base such as triethylamine or pyridine is preferred, and as a recrystallization solvent, benzene or toluene can be used. The reaction temperature is preferably 0°C to room temperature. In reaction formula (2), the sodium salt or potassium salt [′] of phenoxyphenol is converted into isopropanol, acetone, methyl ethyl ketone, benzene,
Suspended in a solvent such as toluene or chloroform, N.N-disubstituted carbamoyl halide []
and react at -20 to 80°C for 2 to 6 hours. In this case, phenoxyphenol and N·N-disubstituted carbamoyl halide may be reacted in the same manner in the presence of a deoxidizing agent such as caustic potash, potassium carbonate, caustic soda, dimethylaniline, triethylamine or pyridine. Through the above reaction, the compound [] of the present invention can be obtained. In reaction formula (3), phenoxyphenol is converted into acetone, methyl ethyl ketone, benzene, toluene,
Alternatively, it is dissolved in chloroform, etc., and reacted with carbonyl dihalide at room temperature to obtain haloformic acid phenoxyphenyl ester [ ].
Since [] is easily decomposed by moisture in the air, it is usually not isolated, but after removing the generated hydrogen halide and excess dissolved carbonyl dihalide in the reaction solution under reduced pressure, it is reacted with twice the molar amount of amine. let After filtering off the generated hydrogen halide salt of the amine and distilling off the solvent, the compound of the present invention [] can be obtained by the same purification method as in reaction formula (1). Next, the manufacturing method of the present invention will be explained in detail with reference to Examples. Example 1 Synthesis of 3-(2-chloro-4-trifluoromethylphenoxy)phenyl N-methylcarbamate 5 g of 3-(2-chloro-4-trifluoromethylphenoxy)phenol was added to 50 ml of anhydrous benzene. Add 3 g of methyl isocyanate and 0.1 ml of triethylamine to this solution and stir at room temperature for 30 minutes.
Stir for hours. After the reaction was completed, the solvent was removed under reduced pressure to obtain an oil, which was recrystallized from a small amount of benzene to obtain 4.6 g of the desired product. Example 2 Synthesis of 3-(2-chloro-4-trifluoromethylphenoxy)phenyl N.N-dimethylcarbamate 7 g of potassium salt of 3-(2-chloro-4-trifluoromethylphenoxy)phenol was The suspension was suspended in 50 ml of methyl ethyl ketone, 4 g of dimethylcarbamic acid chloride was added thereto, and the mixture was stirred at room temperature for 1 hour. After the reaction was completed, the contents were poured into 300 ml of water and extracted with ethyl acetate. The extract phase was washed with water, dried over Glauber's salt, and then ethyl acetate was distilled off, and the residue was purified using column chromatography (silica gel, developing solvent: benzene:ethyl acetate = 50:1). n 18 . 5.8 g of the target product having a D value of 1.5270 at 5 ° C. was obtained. Example 3 Synthesis of 3-(2-chloro-4-trifluoromethylphenoxy)phenyl N/N-diethyl carbamate Dissolve 7 g of 3-(2-chloro-4-trifluoromethylphenoxy)phenol in methyl ethyl ketone. Then, 5 g of potassium carbonate and 5 g of diethylcarbamic acid chloride were added thereto, and the mixture was stirred under heating under reflux for 5 hours. After the reaction was completed, the solid matter was filtered off with suction, methyl ethyl ketone was distilled off, and the residue was purified using column chromatography (silica gel, developing solvent: benzene:ethyl acetate = 50:1). n 18 . 4.5 g of the target product having a D value of 1.5208 at 5 ° C. was obtained. Example 4 11 g of phosgene was absorbed in 100 ml of toluene at 20°C, 28.9 g of 3-(2-chloro-4-trifluoromethylphenoxy)phenol was added, and the liquid temperature was lowered to 20°C.
45% aqueous sodium hydroxide solution while keeping at ~25℃
After 12.5 g was added dropwise, the reaction was completed by stirring for 30 minutes. It was then washed twice with 80 ml of water and once with 100 ml of 2% sodium hydroxide. Thus obtained 3
A toluene solution of -(2-chloro-4-trifluoromethylphenoxy)phenyl chloroformate was maintained at 15 to 20°C and 12.6 g of 50% dimethylamine was added while stirring vigorously. Further, 14 ml of a 20% aqueous sodium hydroxide solution was added dropwise, and the mixture was allowed to react at the same temperature for 1 hour, and then the reaction solution was washed three times with 200 ml of cold water. The toluene layer was then dehydrated over anhydrous sodium sulfate, and the toluene was distilled off at a temperature below 60°C under reduced pressure. The remainder was subjected to column chromatography (silica gel, developing solvent; benzene: n-hexane = 1:
1) and purified by n 18 . 31.2 g of the target product having a D value of 1.5270 at 5 ° C. was obtained. Typical compounds obtained by the above-mentioned production method of the present invention, their physical properties, and elemental analysis values are listed in Table 1 below.

【表】【table】

【表】 本発明化合物の除草剤としての生理作用特性は
次の通りである。(1)イネに対しては直播きをはじ
め、置き苗および移植苗の全ての栽培方式にわた
り著しい高薬量まで無害であり、(2)水田における
強害雑草ノビエをはじめ、一般広葉雑草およびカ
ヤツリグサ科のホタルイおよびミズガヤツリなど
従来防除至難な雑草にも卓効を示し、(3)水稲の田
植前処理、田植直後処理、および移植後10日以上
をすぎたイネおよび雑草の生育期における処理な
ど適用期間が長く、(4)アカザ、メヒシバ、アオビ
ユ、ハキダメギク、スズメノテツポウ、およびハ
ルタデなどの畑雑草に対して土壌処理能力のみな
らず乾田直播や陸稲栽培における茎葉(地上部)
処理能力を持つ。(5)生わら施用の還元性土壌中で
も効果が低減し難い。 以上の如く、本発明化合物は乾田直播や陸稲栽
培における茎葉(地上部)処理能力を持ち、ほと
んど全ての雑草に効力を有し、イネ科のうちイネ
属に対しては全く無害という、驚くべきイネ科属
間選択(イネ科のうちイネ属にのみ無害で小麦
属、メヒシバ属、ノビエ属、およびトウモロコシ
属等は枯死あるいは甚害を示すことをいう)を示
す。本発明化合物を処理した場合に示される薬害
症状は、イネ以外のイネ科雑草に対しては成長点
の細胞分裂伸長を強度に阻害する。その作用は茎
葉処理、土壌処理を問わず、本発明化合物が幼芽
部または根部から吸収されたのち、太陽光線を受
け作用をあらわすという特徴を有する。 なお本発明薬剤は上述の如く水稲田および畑地
のほか、果樹園、桑園、山林その他非農耕地など
に使用でき、その適用範囲は広い。本発明薬剤の
使用方法は一般的には従来の除草剤のそれに準ず
る。すなわち対象植物等により異なるものである
が、一般的には湛水または非湛水の土壌処理また
は全面茎葉処理による方法が適当である。 本発明の除草剤の有効成分である前記一般式で
示される化合物の施用濃度(施用薬量)は対象植
物により異なるが、一般的には3g〜50g/アー
ルの範囲で使用すればよい。 本発明の除草剤を使用する際は、使用場面に応
じて各種の担体と混合し、例えば粉剤、粒剤、錠
剤、水和剤、乳剤等として使用することができ
る。ここにいう担体とは固体、液体の何れでもよ
く、それらの組合せでもよい。その例を列記すれ
ば、カオリナイト、ベントナイト、パイロフイラ
イト、タルク、けいそう土、シリカゲル、炭酸カ
ルシウム、消石灰などの鉱物性粉末、でん粉、ア
ラビアゴムなどの植物性粉末、アルコール類、ケ
トン類、ケロシン、ベンゼン、トルエン、キシレ
ン、シクロヘキサン、メチルナフタレン、ジオキ
サン、ジメチルホルムアミド、ジメチルスルホキ
サイド、トウモロコシ油、o−ジクロルベンゼ
ン、イソホロン等の有機溶剤などであり、さらに
農薬の製剤上使用される補助剤、例えば湿潤剤、
分散剤、固着剤、展着剤などを必要に応じて適宜
使用してもよい。 いずれの製剤もそのまま単独で使用できるのみ
ならず、殺菌剤、殺線虫剤、殺虫剤または植物生
長調整剤などと混合してもよく、また他の除草剤
と混合してもよく、さらには肥料と混合して使用
してもよい。 次に実施例によつて本発明除草剤の代表的製剤
例を示す。 化合物は前記第1表の化合物番号によつて表わ
す。「部」は「重量部」をもつて示す。 実施例 5 化合物番号1 20部 タルク 80部 これらをボールミルでよく粉砕混合して粉剤と
した。 実施例 6 化合物番号2 7部 ベントナイト 88部 リグニソスルホン酸ナトリウム 5部 これらに少量の水を加え造粒して粒剤とした。 実施例 7 化合物番号4 50部 ベントナイト 45部 ポリオキシエチレンアルキルアリールエーテル
5部 これらを混合粉砕して、50%水和剤とした。 次に本発明化合物の効果を試験例により説明す
る。 下記各試験例における表中の数値は作物薬害お
よび雑草害の程度を示すもので、具体的には下記
の通りである。
[Table] The physiological properties of the compounds of the present invention as herbicides are as follows. (1) It is harmless to rice in all cultivation methods, including direct sowing, seedlings, and transplanted seedlings, even at extremely high doses, and (2) it is harmful to rice fields, including common broad-leaved weeds such as Novie, a highly harmful weed in rice fields, and Cyperaceae. It is highly effective against weeds that are conventionally difficult to control, such as Japanese firefly and Japanese cypress. (3) Applicable periods such as pre-planting treatment of paddy rice, treatment immediately after rice transplantation, and treatment during the growing season of rice and weeds more than 10 days after transplantation. (4) Not only does it have soil treatment ability against field weeds such as pigweed, crabgrass, blueberry, leafminer, sparrowgrass, and hartade, but also has excellent stem and leaves (aerial parts) in dry field direct sowing and upland rice cultivation.
Has processing power. (5) The effect is difficult to reduce even in reducing soil when raw straw is applied. As mentioned above, the compound of the present invention has the ability to treat foliage (aerial parts) in dry field direct sowing and upland rice cultivation, is effective against almost all weeds, and is surprisingly harmless to the genus Poaceae of the Poaceae family. Indicates selection among genera of the Poaceae family (in the Poaceae family, only the genus Poaceae is harmless, while the genera Wheat, Poaceae, Novieum, Maize, etc. are withered or severely damaged). The phytotoxic symptoms exhibited when treated with the compound of the present invention strongly inhibit cell division and elongation at the growth point of grasses other than rice. Regardless of whether the compound is treated with foliage or soil, the compound of the present invention is absorbed through the young shoots or roots and then exposed to sunlight. The drug of the present invention can be used not only in rice fields and upland fields as described above, but also in orchards, mulberry orchards, mountain forests, and other non-agricultural lands, and has a wide range of applications. The method of using the agent of the present invention generally follows that of conventional herbicides. That is, although it differs depending on the target plant, etc., generally, a method using flooded or non-flooded soil treatment or whole foliage treatment is appropriate. The application concentration (application amount) of the compound represented by the above general formula, which is the active ingredient of the herbicide of the present invention, varies depending on the target plant, but generally it may be used in the range of 3 g to 50 g/are. When using the herbicide of the present invention, it can be mixed with various carriers depending on the usage situation, and used as a powder, granule, tablet, wettable powder, emulsion, etc., for example. The carrier referred to herein may be either solid or liquid, or a combination thereof. Examples include mineral powders such as kaolinite, bentonite, pyrofluorite, talc, diatomaceous earth, silica gel, calcium carbonate, and slaked lime, starch, vegetable powders such as gum arabic, alcohols, ketones, These include organic solvents such as kerosene, benzene, toluene, xylene, cyclohexane, methylnaphthalene, dioxane, dimethylformamide, dimethyl sulfoxide, corn oil, o-dichlorobenzene, and isophorone, as well as auxiliaries used in the formulation of agricultural chemicals. agents, such as wetting agents,
A dispersant, a fixing agent, a spreading agent, etc. may be used as appropriate. Any of the preparations can not only be used alone, but also be mixed with fungicides, nematicides, insecticides, plant growth regulators, etc., or mixed with other herbicides, and even May be used in combination with fertilizer. Next, typical formulation examples of the herbicide of the present invention will be shown in Examples. Compounds are represented by compound numbers in Table 1 above. "Parts" are expressed as "parts by weight." Example 5 Compound No. 1 20 parts Talc 80 parts These were thoroughly ground and mixed in a ball mill to form a powder. Example 6 Compound No. 2 7 parts Bentonite 88 parts Sodium lignososulfonate 5 parts A small amount of water was added to these and granulated to obtain granules. Example 7 Compound No. 4 50 parts bentonite 45 parts polyoxyethylene alkylaryl ether
5 parts These were mixed and ground to obtain a 50% wettable powder. Next, the effects of the compounds of the present invention will be explained using test examples. The numerical values in the table for each test example below indicate the degree of crop damage and weed damage, and are specifically as follows.

【表】【table】

【表】 試験例 1 (湛水土壌能力検定試験) 1/10000アールポツトに水田土壌を充填し、ノ
ビエ、キカシグサ、ミゾハコベ、ホタルイを播種
し、深さ3cmに湛水する。雑草発芽時、下記有効
成分の所定濃度をピペツトで滴下する。薬剤散布
後、20日目に雑草防除力の程度を観察した。結果
を第2表に示す。化合物は前記第1表の化合物番
号で示す。(以下同様)
[Table] Test example 1 (Flooded soil capacity test) Fill a 1/10000-acre pot with paddy soil, sow wildflowers, Japanese grass, Japanese chickweed, and firefly, and flood to a depth of 3 cm. When weeds germinate, drop the following active ingredients at the specified concentration using a pipette. The degree of weed control ability was observed on the 20th day after the chemical application. The results are shown in Table 2. The compounds are indicated by compound numbers in Table 1 above. (Same below)

【表】【table】

【表】【table】

【表】 試験例 2 供試植物として下記植物を用い次のような方法
で試験した。1/10000アールポツトに水田土壌を
充填する。イネは種子を直播する(表中略記「直
播」)か、2葉期のイネ苗を土壌表層2〜4cmの
深さに移植する(移植)かまたは移植せず土壌表
層に根を固定させる(苗播)の三つの様式を用い
た。また1年生広葉雑草ミゾハコベ、アゼナおよ
びコナギは土壌表層1cmに混入する方法を用い
た。 さらにミズガヤツリおよびマツバイは移植する
方法を用いた。上記播種または移植後ポツトを3
cmに湛水する。雑草発芽時所定濃度の有効成分を
ピペツトで滴下する。薬剤散布後20日目にイネの
薬害と雑草防除力の程度を観察した。結果を第3
表に示す。
[Table] Test Example 2 The following plants were used as test plants and tested in the following manner. Fill a 1/10000 are pot with paddy soil. For rice, seeds are sown directly (abbreviated as "direct sowing" in the table), rice seedlings at the two-leaf stage are transplanted to a depth of 2 to 4 cm from the soil surface (transplanting), or the roots are fixed to the soil surface without transplanting ( Three methods of seedling sowing were used. In addition, annual broad-leaved weeds such as chickweed, azalea, and chinensis were mixed into the soil surface layer of 1 cm. Furthermore, we used a method of transplanting the Japanese cypress and Japanese cypress. After sowing or transplanting the above pots,
Flooded to cm. At the time of weed germination, a predetermined concentration of the active ingredient is dropped with a pipette. On the 20th day after spraying, the damage to rice and the degree of weed control ability were observed. 3rd result
Shown in the table.

【表】 試験例 3 試験例2と同じ供試植物を準備し、ノビエの
2.5葉期、すなわち田植後15日目に所定濃度の薬
剤を施用した。施用後20日にイネの薬害と雑草防
除力の程度を観察した。結果を第4表に示す。
[Table] Test example 3 The same test plants as in test example 2 were prepared, and the
The prescribed concentration of chemicals was applied at the 2.5 leaf stage, ie, 15 days after rice transplantation. 20 days after application, the degree of chemical damage to rice and weed control ability was observed. The results are shown in Table 4.

【表】 試験例 4 試験例2と同じ供試雑草を用い、雑草は播種ま
たは移植し、湛水したのち直ちに所定濃度の有効
成分を施用した。3日後に土壌表層2cmの深さに
イネ苗を移植した。薬剤処理後20日目にイネの薬
害と雑草防除力の程度を視察した。結果を第5表
に示す。
[Table] Test Example 4 Using the same test weeds as in Test Example 2, the weeds were sown or transplanted, and immediately after being flooded with water, the active ingredient at a predetermined concentration was applied. Three days later, the rice seedlings were transplanted to a depth of 2 cm below the soil surface. On the 20th day after chemical treatment, rice damage and weed control ability were observed. The results are shown in Table 5.

【表】 試験例 5 (畑地土壌処理試験) 供試作物としてイネ、コムギ、ダイコンおよび
ダイズを、雑草植物としてメヒシバ、アオビユ、
ハキダメギキおよびハルタデの各種子を含む畑地
土壌を素焼ばちに充填し、下記化合物を下記濃度
で処理した後、処理後30日目に供試作物の薬害状
況および雑草防除力を観察した。結果を第6表に
示す。
[Table] Test Example 5 (Upland soil treatment test) Rice, wheat, radish, and soybean were used as the test crops, and crabgrass, Japanese radish, and soybean were used as weed plants.
Upland soil containing the seeds of Cucumber and Hurtade was filled into clay pots and treated with the following compounds at the concentrations listed below. Thirty days after the treatment, the phytotoxicity and weed control ability of the test crops were observed. The results are shown in Table 6.

【表】 試験例 6 (茎葉接触毒力試験) 1/10000アールポツトに畑地土壌を充填し下記
供試植物の種子を播種し、1cmの覆土をする。こ
れらの種子発芽後、ダイコンでは本葉1〜2葉
期、またコムギでは本葉2〜3葉期に所定濃度の
有効成分水和剤希釈液1mlを全面に噴霧処理し
た。処理後、15日目に供試植物の薬害の程度を観
察した。結果を第7表に示す。
[Table] Test Example 6 (Stem-leaf contact toxicity test) Fill a 1/10,000 are pot with field soil, sow seeds of the following test plants, and cover with 1 cm of soil. After germination of these seeds, 1 ml of a diluted solution of the active ingredient wettable powder at a predetermined concentration was sprayed over the entire surface at the 1st to 2nd true leaf stage for radish and at the 2nd to 3rd true leaf stage for wheat. The degree of phytotoxicity of the test plants was observed on the 15th day after the treatment. The results are shown in Table 7.

【表】 試験例 7 試験例6と同様な方法で下記植物を用い、茎葉
接触毒力試験を行つた。薬剤処理後、15日目に供
試植物の薬害の程度を観察した。結果を第8表に
示す。
[Table] Test Example 7 A foliage contact toxicity test was conducted in the same manner as in Test Example 6 using the following plants. The degree of phytotoxicity of the test plants was observed on the 15th day after the chemical treatment. The results are shown in Table 8.

【表】【table】

Claims (1)

【特許請求の範囲】 1 一般式 (式中R1およびR2はそれぞれ水素原子、低級アル
キル基、フエニル基またはハロゲン置換フエニル
基を示す。)で表わされる化合物。 2 R1が水素原子、R2がメチル基である特許請
求の範囲第1項記載の化合物。 3 R1が水素原子、R2がエチル基である特許請
求の範囲第1項記載の化合物。 4 R1が水素原子、R2がn−プロピル基である
特許請求の範囲第1項記載の化合物。 5 R1が水素原子、R2がi−プロピル基である
特許請求の範囲第1項記載の化合物。 6 R1が水素原子、R2がt−ブチル基である特
許請求の範囲第1項記載の化合物。 7 R1およびR2がメチル基である特許請求の範
囲第1項記載の化合物。 8 R1およびR2がエチル基である特許請求の範
囲第1項記載の化合物。 9 R1が水素原子、R2がフエニル基である特許
請求の範囲第1項記載の化合物。 10 R1が水素原子、R2が3′−クロルフエニル基
である特許請求の範囲第1項記載の化合物。 11 R1が水素原子、R2が3′・4′−ジクロルフエ
ニル基である特許請求の範囲第1項記載の化合
物。 12 R1が水素原子でR2が水素原子またはn−
ブチル基である特許請求の範囲第1項記載の化合
物。 13 R1がメチル基でR2がエチルまたはn−ブ
チル基である特許請求の範囲第1項記載の化合
物。 14 R1およびR2がi−プロピル基である特許
請求の範囲第1項記載の化合物。 15 3−(2−クロル−4−トリフルオルメチ
ルフエノキシ)フエノールと一般式 R2−NCO (式中、R2は低級アルキル基、フエニル基または
ハロゲン置換フエニル基を示す。)で表わされる
イソシアナートとを反応させることを特徴とする
一般式 (式中、R2は前記と同意義である。)で表わされ
る化合物の製造方法。 16 3−(2−クロル−4−トリフルオルメチ
ルフエノキシ)フエノールまたはそのアルカリ金
属塩と一般式 (式中、R1およびR2はそれぞれ水素原子、低級ア
ルキル基、フエニル基またはハロゲン置換フエニ
ル基、Xは塩素原子または臭素原子を示す。)で
表わされるカルバモイルハライドとを反応させる
ことを特徴とする一般式 (式中、R1およびR2は前記と同意義である。)で
表わされる化合物の製造方法。 17 ハロ蟻酸3−(2−クロル−4−トリフル
オルメチルフエノキシ)フエニルエステルと一般
(式中、R1およびR2はそれぞれ水素原子、低級ア
ルキル基、フエニル基またはハロゲン置換フエニ
ル基を示す。)で表わされるアミン化合物とを反
応させることを特徴とする一般式 (式中、R1およびR2は前記と同意義である。)で
表わされる化合物の製造方法。 18 一般式 (式中、R1およびR2は水素原子、低級アルキル
基、フエニル基またはハロゲン置換フエニル基で
ある。)で表わされるカルバミン酸フエノキシフ
エニルエステル誘導体の少くとも一種を有効成分
として含有することを特徴とする除草剤。 19 R1が水素原子、R2がメチル基である特許
請求の範囲第18項記載の除草剤。 20 R1が水素原子、R2がエチル基である特許
請求の範囲第18項記載の除草剤。 21 R1が水素原子、R2がn−プロピル基であ
る特許請求の範囲第18項記載の除草剤。 22 R1が水素原子、R2がi−プロピル基であ
る特許請求の範囲第18項記載の除草剤。 23 R1が水素原子、R2がt−ブチル基である
特許請求の範囲第18項記載の除草剤。 24 R1およびR2がメチル基である特許請求の
範囲第18項記載の除草剤。 25 R1およびR2がエチル基である特許請求の
範囲第18項記載の除草剤。 26 R1が水素原子、R2がフエニル基である特
許請求の範囲第18項記載の除草剤。 27 R1が水素原子、R2が3′−クロルフエニル基
である特許請求の範囲第18項記載の除草剤。 28 R1が水素原子、R2が3′・4′−ジクロルフエ
ニル基である特許請求の範囲第18項記載の除草
剤。 29 R1が水素原子でR2が水素原子またはn−
ブチル基である特許請求の範囲第18項記載の除
草剤。 30 R1がメチル基でR2がエチルまたはn−ブ
チル基である特許請求の範囲第18項記載の除草
剤。 31 R1およびR2がi−プロピル基である特許
請求の範囲第18項記載の除草剤。
[Claims] 1. General formula (In the formula, R 1 and R 2 each represent a hydrogen atom, a lower alkyl group, a phenyl group, or a halogen-substituted phenyl group.) 2. The compound according to claim 1, wherein R 1 is a hydrogen atom and R 2 is a methyl group. 3. The compound according to claim 1 , wherein R 1 is a hydrogen atom and R 2 is an ethyl group. 4. The compound according to claim 1, wherein R 1 is a hydrogen atom and R 2 is an n-propyl group. 5. The compound according to claim 1, wherein R 1 is a hydrogen atom and R 2 is an i-propyl group. 6. The compound according to claim 1 , wherein R 1 is a hydrogen atom and R 2 is a t-butyl group. 7. The compound according to claim 1, wherein R 1 and R 2 are methyl groups. 8. The compound according to claim 1, wherein R 1 and R 2 are ethyl groups. 9. The compound according to claim 1 , wherein R 1 is a hydrogen atom and R 2 is a phenyl group. 10. The compound according to claim 1 , wherein R 1 is a hydrogen atom and R 2 is a 3'-chlorophenyl group. 11. The compound according to claim 1 , wherein R 1 is a hydrogen atom and R 2 is a 3',4'-dichlorophenyl group. 12 R 1 is a hydrogen atom and R 2 is a hydrogen atom or n-
The compound according to claim 1, which is a butyl group. 13. The compound according to claim 1 , wherein R 1 is a methyl group and R 2 is an ethyl or n-butyl group. 14. The compound according to claim 1, wherein R 1 and R 2 are i-propyl groups. 15 3-(2-chloro-4-trifluoromethylphenoxy)phenol represented by the general formula R 2 -NCO (wherein R 2 represents a lower alkyl group, phenyl group or halogen-substituted phenyl group) General formula characterized by reacting with isocyanate A method for producing a compound represented by the formula (wherein R 2 has the same meaning as above). 16 3-(2-chloro-4-trifluoromethylphenoxy)phenol or its alkali metal salt and general formula (In the formula, R 1 and R 2 are a hydrogen atom, a lower alkyl group, a phenyl group, or a halogen-substituted phenyl group, respectively, and X is a chlorine atom or a bromine atom.) general formula to A method for producing a compound represented by the formula (wherein R 1 and R 2 have the same meanings as above). 17 Haloformic acid 3-(2-chloro-4-trifluoromethylphenoxy) phenyl ester and general formula (In the formula, R 1 and R 2 each represent a hydrogen atom, a lower alkyl group, a phenyl group, or a halogen-substituted phenyl group.) A method for producing a compound represented by the formula (wherein R 1 and R 2 have the same meanings as above). 18 General formula (In the formula, R 1 and R 2 are a hydrogen atom, a lower alkyl group, a phenyl group, or a halogen-substituted phenyl group.) Containing at least one type of carbamic acid phenoxy phenyl ester derivative as an active ingredient. A herbicide characterized by 19. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is a methyl group. 20. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is an ethyl group. 21. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is an n-propyl group. 22. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is an i-propyl group. 23. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is a t-butyl group. 24. The herbicide according to claim 18, wherein R 1 and R 2 are methyl groups. 25. The herbicide according to claim 18, wherein R 1 and R 2 are ethyl groups. 26. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is a phenyl group. 27. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is a 3'-chlorophenyl group. 28. The herbicide according to claim 18, wherein R 1 is a hydrogen atom and R 2 is a 3',4'-dichlorophenyl group. 29 R 1 is a hydrogen atom and R 2 is a hydrogen atom or n-
The herbicide according to claim 18, which is a butyl group. 30. The herbicide according to claim 18, wherein R 1 is a methyl group and R 2 is an ethyl or n-butyl group. 31. The herbicide according to claim 18, wherein R 1 and R 2 are i-propyl groups.
JP186879A 1979-01-09 1979-01-09 Phenoxyphenyl carbamate derivative Granted JPS5594353A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP186879A JPS5594353A (en) 1979-01-09 1979-01-09 Phenoxyphenyl carbamate derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP186879A JPS5594353A (en) 1979-01-09 1979-01-09 Phenoxyphenyl carbamate derivative

Publications (2)

Publication Number Publication Date
JPS5594353A JPS5594353A (en) 1980-07-17
JPS6232742B2 true JPS6232742B2 (en) 1987-07-16

Family

ID=11513518

Family Applications (1)

Application Number Title Priority Date Filing Date
JP186879A Granted JPS5594353A (en) 1979-01-09 1979-01-09 Phenoxyphenyl carbamate derivative

Country Status (1)

Country Link
JP (1) JPS5594353A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3837029A1 (en) * 1988-10-31 1990-05-03 Schroff Gmbh HOUSING, IN PARTICULAR ASSEMBLY CARRIERS, WITH SUPPORT RAILS FOR RECEIVING A VARIETY OF PARALLELLY ADDED GUIDE RAILS

Also Published As

Publication number Publication date
JPS5594353A (en) 1980-07-17

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